Before the rise of the 'apps' I was getting quite a bit of my income from Sharewares on the Mac. I stopped when the horde of hipsters started to rely on getting everything and the kitchen sink for $.99.
At the point where I started getting angry emails from users of a freeware because it didn't behave as they'd like, I decided I could spend the time doing something else!
There was quite a nice market for shareware before that, the infrastructure was quite nice with stuff like 'versiontracker', all the emerging 'news' websites. 'Kagi' was /essential/ for that market too, as they'd allowed a normal person to get paid by CC and paypal. Most of the 'users' were also pretty good back then.
Ahhh the good old days blah blah ;-)